Chem 363, Section 2
Exam 1, April 14, 2008
Name: Answer Key Student ID#:_________
1) (5 pts.) Give the correct IUPAC name for the following compound.
Answer:
N,N-Dimethyl-5-bromo-4-phenyl-hexanamide
2) (10 pts.) Draw structures which correspond to the following IUPAC names.
a. Acetic-benzoic-anhydride b. tert-Butyl-octanoate
Answer:
a. b.
3) (20 pts.) Give short answers to the following questions.
a. Put the four studied carboxylic acid derivatives in their increasing order of reactivity.
Answer:
Amides < Esters < Acid anhydrides < Acid halides
b. Which of the two compounds shown below is more reactive toward nucleophilic acyl substitution reactions? Explain your answer.
A B
Answer:
B. Unhindered, accessible carbonyl groups react more readily. Due to inductive effects the carbonyl carbon of compound B is more electrophilic.
c. Give a general example for the alcoholysis of acid halides.
Answer:
d. The mass spectrum of 2-methylbutane is shown below. Which of the
peaks represents the molecular ion (M+)? Which of the peaks
represents the base peak?
Answer:
Molecular ion (M+): the peak at m/z = 72.
Base peak: the peak at m/z = 43.
4) (36 pts.) Complete the following reactions.
a.
Answer:
b.
Answer:
c.
Answer:
d.
Answer:
e.
Answer:
f.
Answer:
g.
Answer:
h.
Answer:
i.
Answer:
j.
Answer:
k.
Answer:
l.
Answer:
5) (6 pts.) Match the mass spectrum with one of the structures given below. Circle the structure.
Answer:
6) (13 points) Using acetylene (ethyne, C2H2) and any alkyl halides as starting materials, synthesize the following compound. Use malonic ester in your synthetic scheme. More than one step will be required. Show all reagents and all intermediate compounds.
Answer:
7) (6 pts.) Write the complete stepwise mechanism for the following reaction. Show all intermediate structures and the electron flow using the curved arrow convention.
Answer:
8) (4 points) Briefly describe four important uses of carboxylic acid derivatives in our everyday lives.
Answer:
Carboxylic acid derivatives are used as solvents, local anesthetics, pain relievers, anti seizure agents, ingredients in perfumes, colorants, etc.
Bonus Question
9) (5 bonus pts.) List the four major reaction types involving carbonyl compounds.
Answer:
1) Nucleophilic addition reactions
2) Nucleophilic acyl substitution reactions
3) α-Substitution reactions
4) Carbonyl condensation reactions